Enstar Group

Enstar Group acquires, manages, and provides services for insurance and reinsurance companies and portfolios in run-off. It serves multinational clients across Bermuda, the US, UK, Australia, and Europe.

Paul O'Shea

Co-Founder and President

6 past transactions

Ruby Reinsurance

Venture Round in 2024
Ruby Re will reinsure RGA business and will not deal with clients directly at first. Ruby Re will receive an automatic quota share of all future qualifying business from RGA (subject to certain criteria, such as achieving underwriting requirements and regulatory clearances).

Inigo

Private Equity Round in 2020
Founded in 2020, Inigo specializes in providing niche insurance and reinsurance products. Its offerings span property, terrorism & political violence, financial lines, and casualty insurance categories.

KaylaRe

Acquisition in 2018
KaylaRe is a Class 4 reinsurer that offers a diversified range of specialty reinsurance. The company was acquired in full by Enstar in 2018.

Companion Property and Casualty Insurance

Acquisition in 2015
Companion Property & Casualty Insurance Group was founded in Columbia, South Carolina in 1984 to provide workers' compensation insurance in South Carolina. At that time, they capitalized on extensive distribution channels with independent agencies, growing throughout the Southeast.

SeaBright Holdings

Acquisition in 2012
SeaBright Holdings, Inc. is a specialty underwriter established in 2003, primarily focused on providing multi-jurisdictional workers' compensation insurance. The company caters to employers with complex workers' compensation needs, offering coverage under various state and federal regulations, as well as common law and negotiated agreements. In addition to its core insurance offerings, SeaBright Holdings also delivers related wholesale brokerage services and integrated managed medical care solutions. Its operations are supported by wholly owned subsidiaries, which include SeaBright Insurance Company, PointSure Insurance Services, Inc., and Paladin Managed Care Services, Inc. Through these entities, SeaBright Holdings aims to address the unique challenges faced by businesses in managing workers' compensation risks.

Unionamerica Holdings

Acquisition in 2008
Unionamerica Holdings Ltd., is a provider of specialty casualty and property insurance and reinsurance services.
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